Water → 4-(Benzyloxy)-2-fluorobenzaldehyde

HRID 1947485Notes

Reaction equation

HRID 1947485 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([F:1])[CH:9]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5872462-Fluoro-4-hydroxybenzaldehyde

Product 1

HCID 121369894-(Benzyloxy)-2-fluorobenzaldehydeYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluoro-4-hydroxy-benzaldehyde (1.0 g, 7.1 mmol) in DMF (70 mL) was added benzylbromide (0.85 mL, 1.2 g, 7.1 mmol) and K2CO3 (1.1 g, 7.9 mmol) and the reaction mixture was stirred (rt, 12 h). The reaction mixture was treated with H2O (50 mL) and filtered to afford the title compound as a colorless solid (1.4 g, 85%). MS (ESI): mass calcd. for C14H11FO2, 230.1; m/z found, 231.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 10.21 (s, 1H), 7.82 (t, J=8.8, 1H), 7.48-7.32 (m, 5H), 6.85 (dd, J=8.8, 2.3, 1H), 6.71 (dd, J=12.3, 2.3, 1H), 5.11 (d, J=14.8, 2H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-cd242cca30394d2d9c27d3522c786c8a
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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